Synthesis of bridgehead-functionalized bicyclo[3.2.1]octanes via intramolecular titanium- and tributylstannane-induced pinacol coupling

被引：12

作者：

Egger, A ^{[1
]}

Hunziker, J ^{[1
]}

Rihs, G ^{[1
]}

Leumann, C ^{[1
]}

机构：

[1] Novartis Pharma AG, CH-4002 Basel, Switzerland

来源：

HELVETICA CHIMICA ACTA | 1998年 / 81卷 / 04期

关键词：

D O I：

10.1002/hlca.19980810323

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of the enantiomerically pure, bridgehead-functionalized bicyclo[3.2.1]octanes 11 and 16, containing a conformationally fixed trihydroxypropyl (aminodihydroxypropyl) unit, as well as the X-ray structure of 11 are described. These compounds are of interest as sugar surrogates in the preparation of DNA analogs. Compounds 11 and 16 became available in 10 and 12 steps, respectively, and in an overall yield of 11 and 4% from D-arabinose via a highly stereoselective pinacol coupling as the key-step.

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页码：734 / 743

页数：10

相关论文

共 19 条

[1]

BARILI PL, 1995, CARBOHYD RES, V43, P278

[2] AN EFFICIENT SYNTHESIS OF ANHYDROALDITOLS AND ALLYL C-GLYCOSIDES [J].

BENNEK, JA ;

GRAY, GR .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (05) :892-897

[3] RING-OPENING OF 2,3-O-BENZYLIDENE, 3,4-O-BENZYLIDENE AND 4,6-O-BENZYLIDENE ACETALS OF PYRANOSIDES BY PHOTOBROMINATION WITH BROMOTRICHLOROMETHANE [J].

CHANA, JS ;

COLLINS, PM ;

FARNIA, F ;

PEACOCK, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (02) :94-96

[4] CONVERSION OF KETONES HAVING DELTA,EPSILON-PI-FUNCTIONS TO CYCLOPENTANOLS BY ZINC-TRIMETHYLCHLOROSILANE [J].

COREY, EJ ;

PYNE, SG .

TETRAHEDRON LETTERS, 1983, 24 (28) :2821-2824

[5] NEW REAGENTS FOR INTERMOLECULAR AND INTRAMOLECULAR PINACOLIC COUPLING OF KETONES AND ALDEHYDES [J].

COREY, EJ ;

DANHEISER, RL ;

CHANDRASEKARAN, S .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (02) :260-265

[6] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287

[7] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES [J].

DESS, DB ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :4155-4156

[8] CONFORMATIONAL STUDIES ON PYRANOID SUGAR DERIVATIVES BY NMR SPECTROSCOPY - CONFORMATIONAL EQUILIBRIA OF PERACETYLATED AND SOME PERBENZOYLATED METHYL D-ALDO-PENTOPYRANOSIDES IN SOLUTION [J].

DURETTE, PL ;

HORTON, D .

CARBOHYDRATE RESEARCH, 1971, 18 (03) :403-&

[9]

FURSTNER A, 1996, ANGEW CHEM, V108, P2582

[10] REACTION OF O-BENZYLIDENE SUGARS WITH N-BROMOSUCCINIMIDE .4. NEIGHBORING-GROUP EFFECTS AND REARRANGEMENTS [J].

HANESSIAN, S ;

PLESSAS, NR .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (04) :1053-+